End-to-end secure communications between a client and a server may be provided by an SSL session connection. The connection may be established across one or more intermediaries, such as network appliances, between the client and the server. A single intermediary between a client and a server may facilitate establishment of an SSL session connection, providing shielding protection to the client via a virtual private network (VPN) for example. In some cases, there are multiple intermediaries, for example for providing data acceleration and other services between two intermediaries across one or more networks. The first intermediary may be in communication with one or more clients while the second intermediary may be in communication with one or more servers.